“When everybody is betting against you, it brings out the best in you,” Mr. Williams, whom his son-in-law calls his mentor, said in an interview. “It’s a good fit for him today and it will be a big part of taking him to where he goes tomorrow.”

Mr. McDonald is now at the helm of a company that racks up less than 15 per cent of Loblaw’s sales. But he’ll be able to make more of a mark at Sears, and then get on recruiters’ Rolodexes for a potentially bigger CEO job in the future Mr. Williams suggested.

Mr. McDonald said he was tempted by the opportunity to broaden his retail leadership skills beyond the grocery sector, while applying his Loblaw lessons to Sears.

Even as a teenager, he had wanted to solve problems. He aspired to be a homicide detective but when he applied to the Ontario Provincial Police, he was rejected for still living at his parents’ home.

He worked at part-time jobs through university, including stocking shelves and pushing carts at the local Loblaws in his hometown of London, Ont. “I’d be out in the parking lot in my big orange Loblaw parka, and colleagues and students would be walking by. … It was tough work.” He resolved then to pave the way for an easier life for his own children.

At the University of Western Ontario, he dated the daughter of Mr. Williams, but didn’t tell him when he applied for a “senior pricing integrity analyst” job at Loblaw in his last year of undergraduate science studies.

At Loblaw, Mr. McDonald moved up the ranks, working over the years with Galen G. Weston, scion of the wealthy family that controls the grocer and, today, its executive chairman and the face of Loblaw in its advertising. “I felt a friendship to him, even though we didn’t interact socially,” Mr. McDonald said. “He was very personable, a great historian of Loblaw and food and the bakery business. He was a confidant. The two of us respected each other.”

Still, the two men have not spoken since Mr. McDonald told Mr. Weston he was leaving, after 18 years with Loblaw in a meeting that lasted just a few minutes. “I felt my loyalty was challenged when, in reality, I felt that 18 years of 120 per cent is all businesses should ask for in terms of loyalty.”

At Sears, Mr. McDonald takes inspiration from the Loblaw boss, who is a year younger, by appearing in the department store’s new Look Report, a chatty take on Sears’ fashions which evokes memories of Loblaw’s iconic Insider Report.

With a penchant for fashion, Mr. McDonald is a poster boy for Sears’ young-minded target customer looking for cooler styles. In the current Look Report, he is featured in a photo clad in a sports jacket and rolled-up jeans over boots; in the upcoming holiday edition, he will appear in a festive velvet blazer, tartan shirt and bow tie.

His broader initiatives are showing small signs of taking off. Amid weak second-quarter results, Sears’ sales gained in major appliances and mattresses.

The CEO makes a point of walking store aisles: In late August, he took three of his four children shopping at the downtown store. He noticed improvements, but the shelves were light on coloured denims and khakis for boys. He reported back to his staff.

“The message to the team is: ‘We haven’t arrived. We still have a long way to go.’”

CURRICULUM VITAE

BEGINNINGS

Born in London, Ont., his parents divorced when he was four; he lived mostly with his mother, a legal office manager, and stepfather, a delivery truck driver; his father was an executive at 3M.

HOME LIFE

He lives in Toronto with his wife Andrea and four children (three boys, aged six, nine and 11; and a two-year-old daughter).

His father-in-law is David Williams, director and former chairman of Shoppers Drug Mart Corp., a former Loblaw executive, and a mentor to Mr. McDonald.

EDUCATION

1994: Bachelor of science from the University of Western Ontario.

2000: MBA from University of Toronto.

CAREER

Spent 18 years at Loblaw, culminating in his 2011 appointment as executive vice-president of the grocer’s conventional division.

Appointed president and CEO of Sears Canada in June, 2011.

PASSIONS

Long-distance running and cycling; has competed in many triathlons and is a two-time Ironman finisher.

Ran the Chicago Marathon this month in three hours and 12 minutes, beating his goal by three minutes.

Runs daily, one way, from his home in Toronto’s Leaside neighbourhood to his office (10 kilometres) and drives the other way.

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